Piperazine-piperidine compounds for use as stabilizers for organic materials
AssigneeCiba-Geigy Corporation
InventorsGraziano Vignali, Valerio Borzatta
Life of this patent
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Abstract
The present invention relates to novel piperazine-piperidine compounds of the general formula (I) ##STR1## in which R.sub.1 is e.g. hydrogen or methyl, R.sub.2 is e.g. ethylene, m is zero or 1 and n is e.g. 1, and when n is 1, A is e.g. 2,2-dimethyl-1-propanoyl, n-butoxycarbonyl, n-tetradecyloxycarbonyl or 2,4-bis[N-butyl-(2',2',6',6'-pentamethyl-4'-piperidyl)amino]triazin-6-yl. The said compounds are effective as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials.
Claims8
A compound of the formula (I) ##STR58## in which R.sub.1 is hydrogen, C.sub.1 -C.sub.8 alkyl, O.cndot., NO, OH, CH.sub.2 CN, C.sub.1 -C.sub.18 alkoxy, C.sub.5 -C.sub.12 cycloalkoxy, C.sub.3 -C.sub.6 alkenyl, C.sub.7 14 C.sub.9 phenylalkyl which is unsubstituted or mono-, di-or tri-substituted on the phenyl by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.8 acyl or C.sub.2 -C.sub.4 alkyl substituted by OH in the 2-, 3- or 4-position, R.sub.2 is C.sub.2 -C.sub.6 alkylene, m is zero or 1, n is 1, 2, 3 or 4 and, if n is 1, A is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.18 alkenyl, C.sub.7 -C.sub.9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C.sub.1 -C.sub.4 alkyl, or A is one of the groups of the formulae (IIa)-(IId) ##STR59## in which X and Y which can be identical or different are a group --OR.sub.6, --SR.sub.6 or ##STR60## where R.sub.6, R.sub.7 and R.sub.8 which can be identical or different are hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.18 alkenyl, phenyl which is unsubstituted or mono-, di- or tri-substituted by C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, C.sub.7 -C.sub.9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkyl substituted in the 2-, 3- or 4-position by OH, by C.sub.1 -C.sub.8 alkoxy or by di-(C.sub.1 -C.sub.4 alkyl)-amino, tetrahydrofurfuryl or a group of the formula (III) ##STR61## where R.sub.9 is as defined for R.sub.1, or ##STR62## is a 5-membered to 7-membered heterocyclic group, R.sub.3 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl which is unsubstituted or mono-, di-or tri-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.18 alkenyl, phenyl which is unsubstituted or mono-, di- or tri-substituted by C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy and/or by an OH group, C.sub.7 -C.sub.9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C.sub.1 -C.sub.4 alkyl and/or by an OH group, p is zero or 1, R.sub.4 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.18 alkenyl or a group of the formula (III) and R.sub.5 is C.sub.1 -C.sub.18 alkyl or phenyl which is unsubstituted or mono-, di- or tri-substituted by C.sub.1 -C.sub.4 alkyl, and, if n is 2, A is C.sub.2 -C.sub. 12 alkylene, C.sub.4 -C.sub.12 alkylene interrupted by 1, 2 or 3 oxygen atoms, 2-hydroxytrimethylene, xylylene or one of the groups of the formulae (IVa)-(IVe) ##STR63## in which q is zero or an integer from 1 to 10, R.sub.10 is a direct bond, C.sub.1 -C.sub.12 alkylene, cyclohexylene or phenylene, R.sub.11 is C.sub.2 -C.sub.12 alkylene, C.sub.4 -C.sub.12 alkylene interrupted by 1, 2 or 3 oxygen atoms, cyclohexylene, cyclohexylenedimethylene, methylenedicyclohexylene, isopropylidenedicyclohexylene, phenylene, isopropylidenediphenylene or xylylene, Z is as defined above for X and Y or is a group of the formula (V) ##STR64## with R.sub.1, R.sub.2 and m being as defined above, D.sub.1 is one of the groups of the formulae (VIa)-(VIc) ##STR65## in which E.sub.1, E.sub.2 and E.sub.3 which can be identical or different are --O-- or ##STR66## R.sub.12 is as defined above for R.sub.11 or C.sub.4 -C.sub.12 alkylene interrupted by 1 or 2 groups ##STR67## R.sub.13 is C.sub.2 -C.sub.6 alkylene, E.sub.4 is >N--(R.sub.13 --E.sub.3).sub.s --, >CH--O-- or ##STR68## r and s which can be identical or different are zero or 1, R.sub.14 is hydrogen or also methyl if r is 1 and E.sub.4 is >CH--O--, R.sub.15 is hydrogen or methyl and R.sub.16 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.7 -C.sub.9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C.sub.1 -C.sub.4 alkyl, or a group of the formula (III), and, if n is 3, A is aliphatic C.sub.4 -C.sub.18 triacyl, aliphatic C.sub.6 -C.sub.18 triacyl containing a trisubstituted nitrogen atom, aromatic C.sub.9 -C.sub.18 triacyl, heterocyclic triacyl containing up to 18 carbon atoms, or A is a group of the formula (VII) ##STR69## in which Z is as defined above and D.sub.2 is one of the groups of the formulae (VIIIa)-(VIIId) ##STR70## in which E.sub.5, E.sub.6, E.sub.7, E.sub.9, E.sub.10 and E.sub.11 which can be identical or different are as defined above for E.sub.1, E.sub.2 and E.sub.3 and, if E.sub.9 and E.sub.10 are --O--, E.sub.11 is also a --CH.sub.2 --O-- group, R.sub.17, R.sub.18 and R.sub.19 which can be identical or different are C.sub.2 -C.sub.6 alkylene, t is zero or 1, R.sub.20, R.sub.21 and R.sub.22 which can be identical or different are as defined above for R.sub.16, E.sub.8 is a direct bond or --CH.sub.2 --, u, v and x which can be identical or different are integers from 2 to 6 and R.sub.23 is hydrogen or C.sub.1 -C.sub.8 alkyl, and, if n is 4, A is aliphatic C.sub.6 -C.sub.18 tetraacyl, aliphatic C.sub.10 -C.sub.18 tetraacyl containing 2 trisubstituted nitrogen atoms, aromatic C.sub.10 -C.sub.18 tetraacyl, cycloaliphatic C.sub.10 -C.sub.22 tetraacyl or a group of the formula (IX) ##STR71## in which Z is as defined above and D.sub.3 is a group of the formula (Xa) or (Xb) ##STR72## in which E.sub.12 is as defined above for E.sub.1, E.sub.2 and E.sub.3, R.sub.24 and R.sub.25 which can be identical or different are C.sub.2 -C.sub.6 alkylene, y is zero or 1 and R.sub.26 is C.sub.4 -C.sub.12 alkanetetrayl.
Dependencies are inferred from the claim text.